3 Stars Hotels in Windsor, Massachusetts from CA $100

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Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Windsor 3-star hotels

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,839 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is CA $114
CA $142 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,266 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is CA $108
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

3. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,005 reviews)
"Nice place to stay"
United States
Michael
The price is CA $156
CA $202 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A building entrance with a large planter with purple flowers and a small tree.

4. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is CA $164
CA $183 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
Room

5. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,006 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $168
CA $188 total
includes taxes & fees
Nov 23 - Nov 24
Hotel Downstreet, an Ascend Collection Hotel
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

6. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,013 reviews)
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."
United States
Lisabeth
The price is CA $223
CA $319 total
includes taxes & fees
Nov 29 - Nov 30
The Red Lion Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

7. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,070 reviews)
"Very nice place beautiful view"
United States
Brian
The price is CA $149
CA $166 total
includes taxes & fees
Nov 17 - Nov 18
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

8. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is CA $151
CA $169 total
includes taxes & fees
Dec 6 - Dec 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.

9. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is CA $240
CA $276 total
includes taxes & fees
Nov 11 - Nov 12
The Cornell Inn, Lenox & The Berkshires
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

10. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
"Nice resort and friendly staff."
United States
Olga
The price is CA $175
CA $195 total
includes taxes & fees
Nov 20 - Nov 21
Jiminy Peak Mountain Resort
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

11. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (689 reviews)
"Great stay!"
United States
Vandhana
The price is CA $177
CA $198 total
includes taxes & fees
Nov 15 - Nov 16
Courtyard by Marriott Lenox Berkshires
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

12. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (529 reviews)
"Great stay"
United States
Ram
The price is CA $228
CA $286 total
includes taxes & fees
Nov 22 - Nov 23
The Porches Inn at Mass MoCA
A fire feature with a metal frame and a brick wall in the background.

13. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
3.0 star property
Williamstown
8.8 out of 10, Excellent, (441 reviews)
"Nicer than your average ~$150 hotels. Clean room, but the details were better than the local Holiday Inn, etc. Would stay again."
United States
Josh
The price is CA $209
CA $233 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Williamstown
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

14. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is CA $191
CA $213 total
includes taxes & fees
Nov 15 - Nov 16
Element by Marriott Lenox Berkshires
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,001 reviews)
"enjoyed our stay"
United States
Mark
The price is CA $138
CA $155 total
includes taxes & fees
Dec 11 - Dec 12
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (717 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is CA $168
CA $187 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.

17. The Ponds at Foxhollow

The Ponds at Foxhollow
3.0 star property
Lenox
8.4 out of 10, Very good, (157 reviews)
"liked it was clean . furniture is dated. Roads need repair . too many potholes"
United States
Anthony
The Ponds at Foxhollow
A two-story house with a porch, a balcony, and a chimney.

18. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
The price is CA $100
CA $181 total
includes taxes & fees
Nov 21 - Nov 22
Blooming Inn
A living room with a fireplace, two sofas, and four black side tables.

19. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is CA $212
CA $237 total
includes taxes & fees
Nov 11 - Nov 12
The Revival House
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

20. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is CA $232
CA $260 total
includes taxes & fees
Dec 3 - Dec 4
Inn at Silver Maple Farm

Top Windsor Hotel Reviews

A building entrance with a large planter with purple flowers and a small tree.
Hotel On North

Hotel On North

Hotel On North
Pittsfield

10/10 Excellent

This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
Canada
alan
Reviewed October 8, 2026
Hotel On North

Find out more about Windsor

The top 3 Stars hotels in Windsor, Windsor may offer some of the best discounts and rates, but these properties are anything but average. Travelers love Windsor 3 Stars hotels for their top quality services, just-like-home amenities, and wallet-friendly prices. You can even get access to fantastic perks like delectable restaurants, so-cool cocktail bars, and spacious fitness centres.

Use the travel tools at Expedia.ca to find a cheap deal on a 3 Stars upscale hotel in Windsor for a first-class experience, or book an inexpensive rate on one of the cheap 3 Stars hotels in Windsor neighbourhoods near the city’s best attractions. We’ll even help you find vacation packages to go with your three star hotel in Windsor. From last-minute work trips to long-awaited family getaways, we offer all the essentials you need to enjoy your jaunt through Windsor.

Frequently Asked Questions

How much does it cost to stay in a 3-star hotel in Windsor?

Take advantage of Expedia's filters to find a good-value 3-star hotel for your upcoming Windsor escape. Simply set your maximum rate with our easy-to-use pricing tool. You can also select the amenities you need, desired neighbourhood and lots more.

  • Search for the lowest price per night right now from CA $100

What is the difference between a 4-star and 3-star hotel in Windsor?

The main difference between a 3- and 4-star hotel in Windsor will be the level of service and availability of creature comforts. 3-star hotels are usually more budget-friendly and provide the amenities and services required to ensure your comfort, such as a gym, WiFi and breakfast. You can count on a bit more at a 4-star hotel — think upmarket décor, premium bathroom products and extra touches like on-site spas.

What is the difference between a 3-star hotel and a motel in Windsor?

Motels usually offer more economical rates compared to hotels, which makes them great if you're exploring around Windsor on a budget. A popular option for overnight stays, these roadside getaways have simply furnished rooms, basic services and ample parking. Opt for a 3-star hotel and you can expect to pay more for additional privacy, comfort and amenities. Guests can make use of things like a lobby, free WiFi and business services at this style of property.

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